Epothilone A

HCID 448799CAS 152044-53-6

기본 정보

표준 SMILES
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@@H]2CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1
InChIKey
HESCAJZNRMSMJG-KKQRBIROSA-N
분자식
C26H39NO6S
평균 분자량
493.7 g/mol
단동위원소 질량
493.24980897

개요

Epothilone A is an epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer). It has a role as a metabolite, an antineoplastic agent, a tubulin modulator and a microtubule-stabilising agent. It is an epoxide and an epothilone.

이름 및 식별자

우선 이름
Epothilone A
IUPAC
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
영어명
Epothilone A
분자식
C26H39NO6S
분자량
493.66

이름 및 동의어

Epothilone A152044-53-6(-)-Epothilone AEpo AEpothilon A51E07YBX96CHEBI:31549DTXSID103322884,17-Dioxabicyclo(14.1.0)heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-((1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (1S,3S,7S,10R,11S,12S,16R)-(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-((E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl)-4,17-dioxabicyclo(14.1.0)heptadecane-5,9-dioneRefChem:137323
이름 더 보기
CS-555CS-1899EpothileEbomycin AEpothilone-Sepothile|||Epo AEpothilone A (Epo A)
DTXCID502833814,17-dioxabicyclo(14,1,0)heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-((1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (1S,3S,7S,10R,11S,12S,16R)-EpoaEpothilone A [MI]MFCD26960884(1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-5,7,9,9-tetramethyl-14-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-13,17-dioxabicyclo[14.1.0]heptadecane-8,12-dione(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

데이터베이스 식별자

CAS
152044-53-6
PubChem CID
448799
DTXSID
DTXSID10332288
ChEMBL
CHEMBL329993
ChEBI
CHEBI:31549
UNII
51E07YBX96

물성

구조 계산 물성

XLogP
4
극성 표면적
137 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
8
회전 가능 결합 수
2
무거운 원자 수
34

실험 및 물리화학적 성질

LipidsPolyketides [PK] -> Macrolides and lactone polyketides [PK04]

물리화학적 성질

녹는점
95 ℃ · 95℃
끓는 점
683.3 · 683.3±55.0 °C(Predicted)
밀도
1.143 · 1.143
저장 조건
-20 °C · -20°C
용해도
클로로포름(약간 용해됨), 에틸아세테이트(약간 용해됨)
물리적 상태
고체

안전 및 규제

유해성 정보

Regulatory Information · 1건

4,17-Dioxabicyclo14.1.0heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (1S,3S,7S,10R,11S,12S,16R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

안전 및 보호

Minimum Risk LevelAcute Oral: 0.01 mg/kg/day (L134)

독성 정보

Treatment · 1건

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health EffectsPBB exposure may cause weight loss, skin disorders (such as acne), nervous and immune systems effects, and effects on the liver, kidneys, and thyroid gland. (L628)
Exposure RoutesOral (L628) ; inhalation (L628) ; dermal (L628)
Toxicity Summary · 1건

The exact mechanism of toxicty of PBBs varies depending on the specific congener. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR). PBBs bind to and activate the AhR, which in turn initiates the transcriptional upregulation of a number of genes, affecting biochemical and endocrine pathways, cell cycle regulation, morphogenesis, oxidative stress response, and various other processes. This results in the numerous toxic responses characteristic of PBBs. Some of the known induced genes include the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2. (L628)

Signs and SymptomsSymptoms of PBB exposure may include nausea, abdominal pain, loss of appetite, joint pain, fatigue, and weakness. (L629)
Carcinogen Classification2A, probably carcinogenic to humans. (L135)

안전 데이터

wgk
3

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

PBBs can be absorbed via oral, inhalation, and dermal routes. Due to their lipophilic nature, PBBs, especially the highly brominated congeners, tend to accumulate in lipid-rich tissues such as the liver, adipose, skin, and breast milk. Certain PBB compounds are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 of the type induced by phenobarbital. The rate of metabolism may depends on the bromine substitution pattern. PBB congeners of low bromine content are transformed into hydroxylated derivatives that are predominately eliminated in the urine. Highly brominated congeners are either retained or excreted unchanged in the feces. (L628)

MeSH Pharmacological Classification · 2건

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.

용도 및 제조

Uses · 1건

PBBs can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. However, the use of PBBs is banned or restricted in most areas due to their toxicity and persistence in the environment. (L628, L629)

응용 분야 · 1건

용도The epothilones are a novel class of antineoplastic agents possessing antitubulin activity. Epothilone A, B isolated from Sorangium cellulosum was associated with cell cycle arrest at G2/M transition and apoptosis that was resisted with overexpression of β-tubulin and P-glycoprotein in human bladder carcinoma cell.

공급사50 곳

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]

추가 설명

정의ChEBI: An epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer).

관련 반응

14건

연결된 노트

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